Isomerization and fragmentation reactions of gaseous dimethyl phenylarsane radical cations and methyl phenylarsenium cations. A study by tandem mass spectrometry and density functional theory calculations

European Journal of Mass Spectrometry

Volumn 12, Issue 3, 2006, Pages 171-180

  Kirchhoff, Dirk ^a   Grützmacher, Hans Friedrich ^a   Grützmacher, Hansjörg ^b  

^a BIELEFELD UNIVERSITY   (Germany)

^b ETH ZURICH   (Switzerland)

Author keywords

Deuteration; DFT calculations; Fragmentation mechanisms; Organoarsenic compounds; Skeletal rearrangements; Tandem mass spectrometry

Indexed keywords

ARSENIC; CATION; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMISTRY; COMPUTER SIMULATION; ELECTROSPRAY MASS SPECTROMETRY; ISOMERISM; METHODOLOGY; TANDEM MASS SPECTROMETRY; THERMODYNAMICS;

ARSENIC; CATIONS; COMPUTER SIMULATION; ISOMERISM; ORGANOMETALLIC COMPOUNDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY; THERMODYNAMICS;

EID: 33747167284     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.802     Document Type: Article

References (22)

1. See M. Gross and R. Caprioli, (Eds), The Encyclopedia of Mass Spectrometry, in particular Vol. 1, Theory and Organic Ion Chemistry and Vol. 4, Theoretical Concepts and Structures and Properties of Gas-Phase Organic ions. Elsevier, Amsterdam, The Netherlands (2004).
2. (a) M.R. Litzow and T.R. Spalding, in Mass Spectrometry of Inorganic and Organometallic Compounds, Series Inorganic Physical Chemistry, Ed by M.F. Lappert, Monograph 3. Elsevier, Amsterdam, The Netherlands (1973);
3. (b) T.R. Spalding, in Mass spectrometry of organometallic compounds in The Chemistry of Functional Groups - The Chemistry of Metal-Carbon Bonds, Ed by F.R. Hartley and S. Patai. John Wiley & Sons, Chichester, UK, pp. 919-969 (1982).
4. .+ (E =) N, P, As, Sb, Bi): Reductive Elimination versus E-C Bond Cleavage," Organometallics 20, 3738 (2001). doi: 10.1021/om0104058
5. NIST Chemistry web book. NIST Standard Reference DatabasE No. 69, March, 2003 Release(http://webbook.nist. gov./chemistry)
6. M. Letzel, D. Kirchhoff, H.-F. Grützmacher, D. Stein and H. Grützmacher, "Isomerization and Fragmentation Reactions of Gaseous Phenylarsane Radical Cations and Phenylarsanyl Cations. A Study by Tandem Mass Spectrometry and Theoretical Calculations," Dalton Trans. 2008 (2006) doi: 10.1039/b514312h
7. 4As-X (X, Y=F, Cl, Br, I). The rôle of non-classical nido structures", Eur. J. Mass Spectrom. 10, 857 (2005). doi: 10.1255/ejms.702
8. D. Kirchhoff, "Tandem massenspektrometrische Untersuchungen: Struktur und Reaktivität von ionisierten Arylelementverbindung der 5. Hauptgruppe", Dissertation, Universität Bielefeld, Germany (1999).
9. Gaussian 03, Revision B.04, Ed by M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle and J.A. Pople. Gaussian, Inc., Pittsburgh, PA, USA (1998).
10. (a) A.D. Becke, Phys. Rev. A 38, 3098 (1988). doi: 10.1103/PhysRevA.38. 3098;
11. (b) A.D. Becke, 98, 1372 (1993);
12. (c) C. Lee, W. Yang and R.G. Parr, Phys. Rev. B 37, 785 (1988). doi: 10.1103/PhysRevB.37.785
13. M. Mohr, H. Zipse, D. Marx and M. Parrinello, J. Phys. Chem. A 101, 8942 (1997). doi: 10.1021/jp972344q
14. M.W. Wong and L. Radom, "Radical Addition to AIkenes: Further Assessment of Theoretical Procedures", J. Phys. Chem. A 102, 2237 (1998). doi: 10.1021/jp973427+
15. K. Hendrick, M. Mickiewicz, N. Roberts, E. Shewchuck and S.B. Wild, Austr. J. Chem. 28, 1473 (1975).
16. .+.
17. E.D. Jemmis and P. von R. Schleyer, "Aromaticity in Three Dimensions. 4. Influence of Orbital Compatibility on the Geometry and Stability of Capped Annulene Rings with Six Interstitial Electrons", J. Am. Chem. Soc. 104, 4781 (1982).
18. H. Schwarz, "On the spin-forbideness of gas phase ion-molecule reactions: a fruitful intersection of experimental and computational studies", Int. J. Mass Spectrom. 237, 75 (2004). doi: 10.1016/j.ijms.2004. 06.006
19. +. Reaction mechanism and dynamics from observation of metastable ion fragmentations and ab initio calculations", Int. J. Mass Spectrom. Ion Proc. 167/168, 117 (1997). doi: 10.1016/80168-1176(97)00037-2
20. V.I. Minkin, M.N. Glujhovtsev and B.Y. Simkin, Atomaticity and Antiaromaticity. John Wiley & Sons Inc., New York, USA (1994).
21. 13C-labelling, " Org. Mass Spectrom. 7, 1091 (1973);
22. (b) K. Weniger, J. Kleimann and H.-F. Grützmacher, "Fragmentation of tert.butylarene radical cations: A comparison with the unimolecular fragmentation of tert-butylbenzene", Eur. Mass Spectrom. 3, 271 (1997).